WO2013042769A1 - Dérivé d'amine aromatique et élément électroluminescent organique utilisant celui-ci - Google Patents

Dérivé d'amine aromatique et élément électroluminescent organique utilisant celui-ci Download PDF

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WO2013042769A1
WO2013042769A1 PCT/JP2012/074232 JP2012074232W WO2013042769A1 WO 2013042769 A1 WO2013042769 A1 WO 2013042769A1 JP 2012074232 W JP2012074232 W JP 2012074232W WO 2013042769 A1 WO2013042769 A1 WO 2013042769A1
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由美子 水木
裕勝 伊藤
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出光興産株式会社
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Definitions

  • the present invention relates to an aromatic amine derivative and an organic electroluminescence device using the same.
  • organic electroluminescence elements using organic substances are expected to be used as solid-state, inexpensive, large-area full-color display elements, and many developments have been made. ing.
  • an organic EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the light emitting layer. When an electric field is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side. Further, the electrons recombine with holes in the light emitting layer to generate an excited state, and energy is emitted as light when the excited state returns to the ground state.
  • Patent Document 1 discloses a light emitting material having dibenzofuran, and although blue light emission with a short wavelength is obtained, the light emission efficiency is low and further improvement has been demanded. .
  • Patent Documents 4 and 5 disclose diaminopyrene derivatives.
  • Patent Document 2 discloses a combination of an anthracene host and an arylamine.
  • Patent Documents 3 to 5 disclose a combination of an anthracene host having a specific structure and a diaminopyrene dopant. Further, Patent Documents 6 to 8 disclose anthracene host materials.
  • Patent Document 9 discloses that an aromatic amine derivative having an arylene group at the center and having a dibenzofuran ring bonded to a nitrogen atom is used as a hole transport material.
  • Patent Document 10 discloses a dibenzofuran ring, a dibenzofuran ring, and a dibenzofuran ring. Although it is disclosed that an aromatic amine derivative in which a thiophene ring, a benzofuran ring, a benzothiophene ring or the like is bonded to a nitrogen atom via an arylene group is used as a hole transport material, there is no example of using it as a light emitting material.
  • Patent Documents 11 to 13 disclose aromatic amine derivatives in which amino groups are bonded to the 1-position and 6-position of pyrene.
  • aromatic amine derivatives described in Patent Document 11 and Patent Document 12 a dibenzofuran ring or a dibenzothiophene ring is bonded to the nitrogen atom of the amino group.
  • These aromatic amine derivatives are used as blue light emitting materials, but further improvement in color purity and luminous efficiency is required for practical use.
  • An object of the present invention is to provide an organic EL element capable of obtaining blue light emission and a useful aromatic amine derivative that can be used for an organic thin film layer of the organic EL element.
  • the following aromatic amine derivative and organic EL device are provided.
  • R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 are each independently Hydrogen atom, Deuterium atom, A halogen atom, A cyano group, A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted alkoxy group having 1 to
  • L 1 and L 2 are each independently Single bond, It is a divalent residue of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a divalent residue of a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • L 3 is It is a divalent residue of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a divalent residue of a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • Ar 1 is a monovalent substituent having the following general formula (3) as a partial structure.
  • X represents an oxygen atom or a sulfur atom.
  • a and B represent a 6-membered ring. The 6-membered ring represented by A and B. In addition, another ring may be condensed.
  • Ar 2 is A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a monovalent substituent having the general formula (3) as a partial structure.
  • X represents an oxygen atom or a sulfur atom.
  • R 11 to R 18 are each independently Hydrogen atom, Deuterium atom, A halogen atom, A cyano group, A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon
  • X 2 represents an oxygen atom or a sulfur atom.
  • X 3 is an oxygen atom, a sulfur atom, NR 31 or CR 32 R 33 .
  • R 21 to R 30 are each independently a hydrogen atom, Deuterium atom, A halogen atom, A cyano group, A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A
  • R 21 to R 30 when Ar 1 is any monovalent residue from the general formula (5) to the general formula (10), among R 21 to R 30 , One is a single bond that binds to L 1 , and when Ar 2 is any monovalent residue from General Formula (5) to General Formula (10), R 21 One of up to R 30 is a single bond bonded to L 2 .
  • R 31 , R 32 and R 33 are each independently A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
  • R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 25 and R 26 , R 27 and R 28 , R 28 and R 29 are used. And a combination of at least one of R 29 and R 30 may form a saturated or unsaturated ring. However, in the general formula (7) and the general formula (8), R 25 and R 26 do not form a ring. )
  • An organic compound layer is provided between the cathode and the anode,
  • the organic compound layer is an organic electroluminescence device including any of the aromatic amine derivatives of the present invention described above.
  • the organic compound layer includes a plurality of organic thin film layers including a light emitting layer, At least one layer of the plurality of organic thin film layers contains any of the aromatic amine derivatives of the present invention described above.
  • At least one of the plurality of organic thin film layers includes any of the aromatic amine derivatives of the present invention described above and an anthracene derivative represented by the following general formula (20). Luminescence element.
  • R 101 to R 108 are each independently Hydrogen atom, A halogen atom, A cyano group, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted condensed ring group having 10 to 30 ring-forming atoms, A group composed of a combination of the monocyclic group and the condensed ring group, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, A substituted or unsubstituted aryloxy having 6 to 30 ring carbon atoms, or a substituted or unsubstituted silyl group.
  • Ar 11 and Ar 12 in the general formula (20) are each independently a substituted or unsubstituted condensed ring group having 10 to 30 ring atoms.
  • One of Ar 11 and Ar 12 in the general formula (20) is a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, and the other is a substituted or unsubstituted ring atom having 10 to 30 atoms.
  • Ar 12 in the general formula (20) is selected from a naphthyl group, a phenanthryl group, a benzoanthryl group, and a dibenzofuranyl group, and Ar 11 is an unsubstituted phenyl group, the monocyclic group, or the condensed ring group.
  • Ar 12 in the general formula (20) is a substituted or unsubstituted condensed ring group having 10 to 30 ring-forming atoms, and Ar 11 is an unsubstituted phenyl group. .
  • Ar 11 and Ar 12 in the general formula (20) are each independently a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms.
  • Ar 11 and Ar 12 in the general formula (20) are each independently a substituted or unsubstituted phenyl group.
  • Ar 11 in the general formula (20) is an unsubstituted phenyl group
  • Ar 12 is a phenyl group having at least one of the monocyclic group and the condensed ring group as a substituent. Electroluminescence element.
  • Ar 11 and Ar 12 in the general formula (20) are each independently a phenyl group having at least one of the monocyclic group and the condensed ring group as a substituent.
  • an organic EL element capable of obtaining blue light emission and a useful aromatic amine derivative that can be used for an organic thin film layer of the organic EL element.
  • the aromatic amine derivative of the present invention is represented by the general formula (1).
  • R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 in the general formula (1) will be described.
  • Examples of the aryl group having 6 to 30 ring carbon atoms in the general formula (1) include a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, Benzanthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, pyrenyl group, 1-chrysenyl group, 2-chrysenyl group, 3-chrysenyl group, 4- Chrysenyl group, 5-chrenyl group, 6-chrenyl group, benzo [c] phenanthryl group, benzo [g] chrysenyl group, 1-triphenylenyl group, 2-triphenylenyl group, 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group Group, 4-fluorenyl group, 9-fluoren
  • the aryl group in the general formula (1) preferably has 6 to 20 ring carbon atoms, more preferably 6 to 12 carbon atoms.
  • a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a terphenyl group, and a fluorenyl group are particularly preferable.
  • the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms in the general formula (1) is present at the 9-position carbon atom. It is preferably substituted.
  • heterocyclic group having 5 to 30 ring atoms in the general formula (1) examples include pyrrolyl group, pyrazinyl group, pyridyl group, pyrimidinyl group, triazinyl group, pyridazinyl group, indolyl group, isoindolyl group, imidazolyl group, Pyrazolyl group, triazolyl group, benzoimidazolyl group, indazolyl group, imidazopyridinyl group, benzotriazolyl group, furyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, thienyl group, benzothiophenyl group, dibenzo Thiophenyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl
  • the number of ring-forming atoms of the heterocyclic group in the general formula (1) is preferably 5-20, and more preferably 5-14.
  • 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3- A dibenzothiophenyl group, a 4-dibenzothiophenyl group, a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, and a 9-carbazolyl group are preferable.
  • the alkyl group having 1 to 30 carbon atoms in the general formula (1) may be linear, branched or cyclic.
  • Examples of the linear or branched alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n- Hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n- Hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpenty
  • cyclic alkyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and 2- And norbornyl group.
  • the linear or branched alkyl group in the general formula (1) preferably has 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms.
  • the cycloalkyl group preferably has 3 to 10 ring carbon atoms, and more preferably 5 to 8 carbon atoms.
  • a cyclopentyl group and a cyclohexyl group are preferable.
  • halogenated alkyl group in which the alkyl group is substituted with a halogen atom include those in which the alkyl group having 1 to 30 carbon atoms is substituted with one or more halogen groups. Specific examples include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, and a trifluoromethylmethyl group.
  • the alkenyl group having 2 to 30 carbon atoms in the general formula (1) may be linear, branched or cyclic, such as vinyl, propenyl, butenyl, oleyl, eicosapentaenyl, docosahexa Examples include enyl, styryl, 2,2-diphenylvinyl, 1,2,2-triphenylvinyl, 2-phenyl-2-propenyl and the like.
  • a vinyl group is preferable.
  • the alkynyl group having 2 to 30 carbon atoms in the general formula (1) may be linear, branched or cyclic, and examples thereof include ethynyl, propynyl, 2-phenylethynyl and the like. Of the alkynyl groups described above, an ethynyl group is preferred.
  • Examples of the alkylsilyl group having 3 to 30 carbon atoms in the general formula (1) include a trialkylsilyl group having an alkyl group exemplified as the alkyl group having 1 to 30 carbon atoms, specifically, a trimethylsilyl group, Triethylsilyl, tri-n-butylsilyl, tri-n-octylsilyl, triisobutylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyl-n-propylsilyl, dimethyl-n-butylsilyl, dimethyl -T-butylsilyl group, diethylisopropylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triisopropylsilyl group and the like.
  • the three alkyl groups may be the same or different from each other.
  • alkyldiarylsilyl group examples include an alkyldiarylsilyl group having one alkyl group exemplified for the alkyl group having 1 to 30 carbon atoms and two aryl groups having 6 to 30 ring carbon atoms. .
  • the alkyldiarylsilyl group preferably has 13 to 30 carbon atoms.
  • the two aryl groups may be the same or different.
  • Examples of the triarylsilyl group include a triarylsilyl group having three aryl groups having 6 to 30 ring carbon atoms.
  • the carbon number of the triarylsilyl group is preferably 18-30.
  • the three aryl groups may be the same or different from each other.
  • the alkoxy group having 1 to 30 carbon atoms in the general formula (1) is represented as —OY.
  • Y include the alkyl group having 1 to 30 carbon atoms.
  • the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group.
  • the halogenated alkoxy group in which the alkoxy group is substituted with a halogen atom include those in which the alkoxy group having 1 to 30 carbon atoms is substituted with one or more halogen groups.
  • the aralkyl group having 6 to 30 ring carbon atoms in the general formula (1) is represented by —Y—Z.
  • Y include an alkylene group corresponding to the alkyl group having 1 to 30 carbon atoms.
  • Z include the above aryl groups having 6 to 30 ring carbon atoms.
  • This aralkyl group has 7 to 30 carbon atoms (the aryl moiety has 6 to 30, preferably 6 to 20, more preferably 6 to 12 carbon atoms), and the alkyl moiety has 1 to 30 carbon atoms (preferably 1 to 20 carbon atoms). More preferably, it is 1 to 10, and more preferably 1 to 6).
  • Examples of the aralkyl group include benzyl group, 2-phenylpropan-2-yl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, and phenyl-t-butyl.
  • ⁇ -naphthylmethyl group 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ - Naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, 1-pyrrolylmethyl group, 2- (1-pyrrolyl) ethyl group, p-methylbenzyl group, m -Methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromine Benzyl group, m
  • the aryloxy group having 6 to 30 ring carbon atoms in the general formula (1) is represented by —OZ.
  • Z include the above aryl group having 6 to 30 ring carbon atoms, or a monocyclic group and a condensed ring group described later.
  • Examples of the aryloxy group include a phenoxy group.
  • halogen atom in the general formula (1) examples include fluorine, chlorine, bromine, iodine, and the like, preferably a fluorine atom.
  • ring-forming carbon means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring.
  • Ring-forming atom means a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring).
  • examples of the substituent include an aryl group, a heterocyclic group, an alkyl group (a linear or branched alkyl group, a cycloalkyl group, a halogenated alkyl group) as described above, In addition to alkenyl, alkynyl, alkylsilyl, arylsilyl, alkoxy, halogenated alkoxy, aralkyl, aryloxy, halogen, deuterium, cyano, hydroxyl, nitro, carboxy, etc. Is mentioned.
  • an aryl group, a heterocyclic group, an alkyl group, a halogen atom, an alkylsilyl group, an arylsilyl group, a cyano group, and a deuterium atom are preferable, and more preferable in the description of each substituent.
  • the specific substituents are preferred.
  • “Unsubstituted” in the case of “substituted or unsubstituted” means that a hydrogen atom is substituted. In the compound described below or a partial structure thereof, the case of “substituted or unsubstituted” is the same as described above.
  • R 1 and R 6 are represented by the general formula (2).
  • L 1 and L 2 are each independently a single bond, a substituted or unsubstituted divalent residue of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted group. This is a divalent residue of a heterocyclic group having 5 to 30 ring atoms.
  • L 3 represents a divalent residue of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a divalent residue of a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. is there.
  • the divalent residue of the aryl group having 6 to 30 ring carbon atoms is the ring in R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 in the general formula (1).
  • Examples thereof include a divalent group derived from an aryl group having 6 to 30 carbon atoms.
  • the divalent residue of the heterocyclic group having 5 to 30 ring atoms is represented by R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 in the general formula (1).
  • a divalent group derived from a heterocyclic group having 5 to 30 ring atoms is represented by R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 in the general formula (1).
  • a divalent group derived from a heterocyclic group having 5 to 30 ring atoms is represented by R 2 , R 3 , R 4 , R 5 , R
  • Ar 1 is a monovalent substituent having the general formula (3) as a partial structure.
  • X is an oxygen atom or a sulfur atom.
  • a and B represent a 6-membered ring. Another ring may be further condensed to the 6-membered ring represented by A and B.
  • Ar 2 represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or the general formula ( It is a monovalent substituent having 3) as a partial structure.
  • the aryl group and heterocyclic group of Ar 2 are the same as those described in R 1 to R 10 in the general formula (1).
  • the monovalent substituent having the general formula (3) as a partial structure is preferably a monovalent residue of the general formula (4).
  • X is an oxygen atom or a sulfur atom.
  • R 11 to R 18 are each independently R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 in the general formula (1). This is the same as that described in.
  • Ar 1 is a monovalent residue of the general formula (4), one of R 11 to R 18 is bonded to L 1 .
  • R 11 and R 12, R 12 and R 13, R 13 and R 14, R 15 and R 16, R 16 and R 17 and R 17 and R 18, at least one One or a combination may form a saturated or unsaturated ring.
  • Examples of the case where such a ring may be formed in the general formula (4) include the following general formulas (4E), (4F), and (4G).
  • R 11 to R 20 are independently from R 2 to R 5 and R 7 to R 10 in the general formula (1). The same as described.
  • the monovalent substituent having the general formula (3) as a partial structure is any of the monovalent residues from the general formula (5) to the general formula (10). It is preferable that In the general formula (5) to general formula (10), X 2 is an oxygen atom or a sulfur atom. In the general formula (5) to general formula (10), X 3 is an oxygen atom, a sulfur atom, NR 31 or CR 32 R 33 .
  • NR 31 is a combination of R 31 and a nitrogen atom (N).
  • CR 32 R 33 is obtained by bonding R 32 and R 33 to a carbon atom (C).
  • R 21 to R 30 are each independently R 2 , R 3 , R 4 , R 5 , R 7 , R in the general formula (1). 8 , R 9 and the substituent described for R 10 or a hydrogen atom.
  • Ar 1 is any monovalent residue from the general formula (5) to the general formula (10)
  • R 21 to R 30 One is a single bond that binds to L 1
  • Ar 2 is any monovalent residue from General Formula (5) to General Formula (10)
  • R 21 One of up to R 30 is a single bond bonded to L 1 .
  • the structure from the general formula (5) to the general formula (10) is, for example, from the following general formula (5A) to the general formula (5J).
  • the general formula (9A) is as well as the following general formula (10A) to general formula (10J).
  • the general formula (5A) indicates that the portion of R 21 in the general formula (5) is a single bond, and does not indicate that it is a methyl group.
  • R 31 , R 32 and R 33 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted or unsubstituted.
  • the aryl group, heterocyclic group and alkyl group of R 31 , R 32 and R 33 are R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 in the general formula (1). This is the same as that described in.
  • R 1 and R 6 in the general formula (1) are preferably represented by the general formula (2).
  • the aromatic amine derivative has the following general formula: The structure is represented by (1A).
  • aromatic amine derivative of the present invention in general formula (1A), R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 , L 1 to L 3 , And aromatic amine derivatives when Ar 1 to Ar 2 are as shown in Tables 1 to 22.
  • “ ⁇ ” in L 1 to L 3 represents a single bond.
  • a chemical formula (CH 3 , Ph, CN, benzene ring, etc.) is described at the end of the line extending from the ring structure toward the outside. Those not present represent a single bond and do not represent a methyl group.
  • L 3 represents a 1,4-phenylene group.
  • Ar 1 represents a single bond at the 4-position of the dibenzofuran ring, that is, a 4-dibenzofuranyl group.
  • Ar 2 represents a phenyl group.
  • the compounds represented by the general formula (2) have the same structure as each other.
  • the present invention is not limited to this. It may be a compound having a different structure.
  • the aromatic amine derivative of the present invention can be used as a material for an organic EL device.
  • the material for an organic EL device may contain the aromatic amine derivative of the present invention alone or may contain other compounds.
  • the material for organic EL elements containing the aromatic amine derivative of the present invention can be used as a dopant material, for example.
  • a material for an organic EL device including an anthracene derivative represented by the general formula (20) can be given.
  • the organic EL element material which contains the pyrene derivative represented by following General formula (30) with the aromatic amine derivative of this invention instead of this anthracene derivative is mentioned.
  • the organic EL element material containing the aromatic amine derivative of this invention, the anthracene derivative represented by the said General formula (20), and the pyrene derivative represented by the following general formula (30) is mentioned.
  • the organic EL device of the present invention includes an organic compound layer between a cathode and an anode.
  • the aromatic amine derivative of the present invention is contained in this organic compound layer.
  • an organic compound layer is formed using the material for organic EL elements containing the aromatic amine derivative of this invention.
  • the organic compound layer has at least one organic thin film layer composed of an organic compound. At least one of the organic thin film layers contains the aromatic amine derivative of the present invention alone or as a component of a mixture.
  • the organic thin film layer may contain the inorganic compound. At least one of the organic thin film layers is a light emitting layer.
  • the organic compound layer may be composed of, for example, a single light emitting layer, such as a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole barrier layer, an electron barrier layer, etc. You may have the layer employ
  • the aromatic amine derivative of the present invention is contained alone or as a component of the mixture in at least one of the layers.
  • the light emitting layer contains the aromatic amine derivative of the present invention.
  • the light emitting layer can be composed of only an aromatic amine derivative, or can be composed of an aromatic amine derivative as a host material or a dopant material.
  • the configuration (d) is preferably used, but it is of course not limited thereto.
  • the “light emitting layer” is an organic layer having a light emitting function, and includes a host material and a dopant material when a doping system is employed.
  • the host material mainly has a function of encouraging recombination of electrons and holes and confining excitons in the light emitting layer, and the dopant material efficiently emits excitons obtained by recombination. It has a function.
  • hole injection / transport layer means “at least one of a hole injection layer and a hole transport layer”
  • electron injection / transport layer means “an electron injection layer and an electron transport layer”. "At least one of them”.
  • the positive hole injection layer is provided in the anode side.
  • the electron injection layer is provided in the cathode side.
  • the hole injection layer, the light emitting layer, and the electron injection layer may each be formed of two or more layers.
  • the layer that injects holes from the electrode is a hole injection layer
  • the layer that receives holes from the hole injection layer and transports holes to the light emitting layer is a hole transport layer.
  • a layer that injects electrons from an electrode is referred to as an electron injection layer
  • a layer that receives electrons from the electron injection layer and transports electrons to a light emitting layer is referred to as an electron transport layer.
  • the organic EL element can prevent the brightness
  • a light emitting material, a doping material, a hole injection material, and an electron injection material can be used in combination.
  • light emission luminance and light emission efficiency may be improved.
  • Each of these layers is selected and used depending on factors such as the energy level of the material, heat resistance, and adhesion to the organic layer or metal electrode.
  • the organic EL element 1 includes a transparent substrate 2, an anode 3, a cathode 4, and an organic compound layer 10 disposed between the anode 3 and the cathode 4.
  • the organic compound layer 10 includes a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and an electron injection layer 9 in order from the anode 3 side.
  • the light emitting layer of the organic EL element has a function of providing a field for recombination of electrons and holes and connecting this to light emission.
  • the aromatic amine derivative of the present invention is contained in at least one layer of the organic thin film layer, and is further represented by the anthracene derivative represented by the general formula (20) and the following general formula (30). It is preferable that at least one of pyrene derivatives is contained.
  • the light emitting layer contains the aromatic amine derivative of the present invention as a dopant material and an anthracene derivative represented by the above formula (20) as a host material.
  • Ar 11 and Ar 12 are each independently a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms or a condensed or unsubstituted ring atom having 10 to 30 ring atoms. It is a group composed of a ring group or a combination of the monocyclic group and the condensed ring group.
  • the monocyclic group is a group composed of only a ring structure having no condensed structure.
  • the number of ring-forming atoms of the monocyclic group is 5 to 30, preferably 5 to 20.
  • the monocyclic group include aromatic groups such as phenyl group, biphenyl group, terphenyl group, and quarterphenyl group, and heterocyclic groups such as pyridyl group, pyrazyl group, pyrimidyl group, triazinyl group, furyl group, and thienyl group. Is mentioned. Among these, a phenyl group, a biphenyl group, and a terphenyl group are preferable.
  • the condensed ring group is a group in which two or more ring structures are condensed.
  • the number of ring-forming atoms of the fused ring group is 10-30, preferably 10-20.
  • Examples of the condensed ring group include naphthyl group, phenanthryl group, anthryl group, chrysenyl group, benzoanthryl group, benzophenanthryl group, triphenylenyl group, benzochrysenyl group, indenyl group, fluorenyl group, 9,9-dimethylfluorene group.
  • Nyl group benzofluorenyl group, dibenzofluorenyl group, fluoranthenyl group, benzofluoranthenyl group and other condensed aromatic ring groups, benzofuranyl group, benzothiophenyl group, indolyl group, dibenzofuranyl group, Examples thereof include condensed heterocyclic groups such as a dibenzothiophenyl group, a carbazolyl group, a quinolyl group, and a phenanthrolinyl group.
  • naphthyl group phenanthryl group, anthryl group, 9,9-dimethylfluorenyl group, fluoranthenyl group, benzoanthryl group, dibenzothiophenyl group, dibenzofuranyl group, and carbazolyl group are preferable.
  • alkyl group, silyl group, alkoxy group, aryloxy group, aralkyl group, and halogen atom from R 101 to R 108 in the general formula (20) include R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 are the same as those described above, and the cycloalkyl group is the same as that exemplified above. Further, the case of “substituted or unsubstituted” in these substituents is the same as described above.
  • the preferable specific example in General formula (20) is given below.
  • Ar 11 and Ar 12 in the general formula (20) and preferable substituents of “substituted or unsubstituted” from R 101 to R 108 are monocyclic groups, condensed ring groups, alkyl groups, cycloalkyl groups, silyl groups. , An alkoxy group, a cyano group, and a halogen atom (particularly fluorine). Particularly preferred are a monocyclic group and a condensed ring group, and preferred specific substituents are the same as those in the general formula (20) and the general formula (1).
  • the anthracene derivative represented by the general formula (20) is preferably any of the following anthracene derivatives (A), (B), and (C), and is selected according to the configuration of the organic EL element to be applied and the required characteristics. .
  • Anthracene derivatives (A) In the anthracene derivative (A), Ar 11 and Ar 12 in the general formula (20) are substituted or unsubstituted condensed ring groups having 10 to 30 ring atoms.
  • the anthracene derivative (A) is divided into a case where Ar 11 and Ar 12 are the same substituted or unsubstituted condensed ring group and a case where Ar 11 and Ar 12 are different substituted or unsubstituted condensed ring groups. be able to.
  • Ar 11 and Ar 12 are different, the case where the substitution positions are different is also included.
  • an anthracene derivative in which Ar 11 and Ar 12 in the general formula (20) are different substituted or unsubstituted condensed ring groups is particularly preferable.
  • preferred specific examples of the condensed ring group in Ar 11 and Ar 12 in the general formula (20) are as described above. Of these, a naphthyl group, a phenanthryl group, a benzoanthryl group, a 9,9-dimethylfluorenyl group, and a dibenzofuranyl group are preferable.
  • Anthracene derivatives (B)
  • one of Ar 11 and Ar 12 in the general formula (20) is a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, and the other is a substituted or unsubstituted ring.
  • Ar 12 is selected from a naphthyl group, a phenanthryl group, a benzoanthryl group, a 9,9-dimethylfluorenyl group, and a dibenzofuranyl group, and Ar 11 is unsubstituted.
  • anthracene derivative (B) includes a case where Ar 12 is a substituted or unsubstituted condensed ring group having 10 to 30 ring atoms and Ar 11 is an unsubstituted phenyl group.
  • the condensed ring group is particularly preferably a phenanthryl group, a 9,9-dimethylfluorenyl group, a dibenzofuranyl group, or a benzoanthryl group.
  • Anthracene derivatives (C) are each independently a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms.
  • a preferred form of the anthracene derivative (C) includes a case where Ar 11 and Ar 12 are each independently a substituted or unsubstituted phenyl group.
  • Ar 11 is an unsubstituted phenyl group
  • Ar 12 is a phenyl group having at least one of the monocyclic group and the condensed ring group as a substituent.
  • Ar 11 and Ar 12 are each independently a phenyl group having at least one of the monocyclic group and the condensed ring group as a substituent.
  • the monocyclic group as a substituent is more preferably a phenyl group or a biphenyl group
  • the condensed ring group as a substituent is a naphthyl group, a phenanthryl group, a 9,9-dimethylfluorenyl group, a dibenzofuranyl group, a benzoan group.
  • a tolyl group is more preferred.
  • anthracene derivative represented by the general formula (20) include the following. However, the present invention is not limited to the anthracene derivatives having these structures.
  • R 101 and R 105 are each independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted group.
  • a condensed ring group having 10 to 30 ring atoms a group composed of a combination of a monocyclic group and a condensed ring group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted ring forming carbon
  • Ar 51 and Ar 54 each independently represent a substituted or unsubstituted monocyclic divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted ring atom having 10 atoms. It is a fused ring divalent residue of ⁇ 30.
  • Ar 52 and Ar 55 are each independently a single bond, a substituted or unsubstituted monocyclic divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted ring. It is a condensed ring divalent residue having 10 to 30 atoms.
  • Ar 51 represents a substituted or unsubstituted monocyclic divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted condensed ring divalent having 10 to 30 ring atoms.
  • Ar 52 and Ar 55 each independently represent a single bond, a substituted or unsubstituted monocyclic divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted ring. It is a condensed ring divalent residue having 10 to 30 atoms.
  • Ar 53 and Ar 56 each independently represent a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted ring atom having 10 atoms. 30 to 30 condensed ring groups. All or some of the hydrogen atoms in the general formula (20B) may be deuterium atoms.
  • Ar 52 represents a substituted or unsubstituted monocyclic divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted condensed ring divalent having 10 to 30 ring atoms.
  • Ar 55 is a single bond, a substituted or unsubstituted monovalent divalent residue having 5 to 30 ring atoms, or a condensed having 10 to 30 ring atoms that are substituted or unsubstituted. It is a ring divalent residue.
  • Ar 53 and Ar 56 each independently represent a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted ring atom having 10 atoms. 30 to 30 condensed ring groups. All or some of the hydrogen atoms in the general formula (20C) may be deuterium atoms.
  • Ar 52 represents a substituted or unsubstituted monovalent divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted condensed ring divalent having 10 to 30 ring atoms.
  • Ar 55 represents a single bond, a substituted or unsubstituted monovalent divalent residue having 5 to 30 ring atoms, or a condensed having 10 to 30 ring atoms that are substituted or unsubstituted. It is a ring divalent residue.
  • Ar 53 and Ar 56 are each independently a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted ring atom having 10 atoms. 30 to 30 condensed ring groups. All or some of the hydrogen atoms in the general formula (20D) may be deuterium atoms.
  • Ar 52 and Ar 55 are each independently a single bond, a substituted or unsubstituted monocyclic divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted ring. It is a condensed ring divalent residue having 10 to 30 atoms.
  • Ar 53 and Ar 56 each independently represent a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted ring atom having 10 atoms. 30 to 30 condensed ring groups. All or some of the hydrogen atoms in the general formula (20E) may be deuterium atoms.
  • the present invention is not limited to the anthracene derivatives having these structures.
  • the line extending from the 9th position of the fluorene ring represents a methyl group, that is, the fluorene ring is 9 , 9-dimethylfluorene ring.
  • a line extending in a cross shape outward from the ring structure is a tertiary butyl group. Represents.
  • a line extending from the silicon atom (Si) represents a methyl group, that is, the substituent having the silicon atom represents a trimethylsilyl group.
  • At least one of the organic thin film layers comprises an aromatic amine derivative represented by the general formula (1) and a pyrene derivative represented by the following general formula (30).
  • the form to contain is mentioned.
  • the light emitting layer preferably contains an aromatic amine derivative as a dopant material and a pyrene derivative as a host material.
  • Ar 111 and Ar 222 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • L 1 and L 2 each independently represent a substituted or unsubstituted divalent aryl group or heterocyclic group having 6 to 30 ring carbon atoms.
  • m is an integer of 0 to 1
  • n is an integer of 1 to 4
  • s is an integer of 0 to 1
  • t is an integer of 0 to 3.
  • L 1 or Ar 111 is bonded to any one of 1 to 5 positions of pyrene
  • L 2 or Ar 222 is bonded to any of 6 to 10 positions of pyrene.
  • Ar 111 and Ar 222 in the general formula (30) and the case of “substituted or unsubstituted” in the substituents of L 1 and L 2 are the same as described above.
  • L 1 and L 2 in the general formula (30) are preferably A substituted or unsubstituted phenylene group, A substituted or unsubstituted biphenylene group, A substituted or unsubstituted naphthylene group, It is selected from a substituted or unsubstituted terphenylene group, a substituted or unsubstituted fluorenylene group, and a divalent aryl group composed of a combination of these groups.
  • M in the general formula (30) is preferably an integer of 0 to 1.
  • n is preferably an integer of 1 to 2.
  • s is preferably an integer of 0 to 1.
  • T in the general formula (30) is preferably an integer of 0 to 2.
  • the aryl groups of Ar 111 and Ar 222 in the general formula (30) are described in R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 in the general formula (1). It is the same as what I did.
  • the aryl group include a phenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a biphenyl group, an anthryl group, and a pyrenyl group.
  • the aromatic amine derivative of the present invention in addition to the light emitting layer, a hole injection layer, a hole transport layer, It can also be used for an electron injection layer and an electron transport layer.
  • the organic thin film layer contains the aromatic amine derivative of the present invention as a dopant material
  • the content of the aromatic amine derivative is preferably 0.1% by mass or more and 20% by mass or less, and preferably 1% by mass or more and 10% by mass. The following is more preferable.
  • the organic EL element of the present invention is produced on a light-transmitting substrate.
  • the translucent substrate is a substrate that supports the organic EL element, and is preferably a smooth substrate having a light transmittance in the visible region of 400 nm or more and 700 nm or less of 50% or more.
  • the substrate preferably further has mechanical and thermal strength.
  • a glass plate, a polymer plate, etc. are mentioned.
  • the glass plate include those using soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz and the like as raw materials.
  • the polymer plate include those using polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, polysulfone and the like as raw materials.
  • a polymer film can also be used as the substrate.
  • a material having a work function larger than 4 eV is suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum Further, palladium, etc. and their alloys, metal oxides such as tin oxide and indium oxide used for ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole are used.
  • the anode is produced by forming a thin film of these conductive materials by a method such as vapor deposition or sputtering.
  • the light transmittance in the visible region of the anode be greater than 10%.
  • the sheet resistance of the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness of the anode depends on the material, it is usually selected in the range of 10 nm to 1 ⁇ m, preferably 10 nm to 200 nm.
  • the conductive material used for the cathode of the organic EL device of the present invention those having a work function smaller than 4 eV are suitable, and magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum , Lithium fluoride and the like and alloys thereof are used, but not limited thereto.
  • alloys include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto.
  • the ratio of the alloy is controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, etc., and is selected to an appropriate ratio.
  • the cathode can be produced by forming a thin film by a method such as vapor deposition or sputtering.
  • the aspect which takes out light emission from a cathode side is also employable.
  • the light transmittance in the visible region of the cathode be greater than 10%.
  • the sheet resistance of the cathode is preferably several hundred ⁇ / ⁇ or less.
  • the layer thickness of the cathode depends on the material, but is usually selected in the range of 10 nm to 1 ⁇ m, preferably 50 nm to 200 nm.
  • the anode and the cathode may be formed with a layer structure of two or more layers if necessary.
  • the organic EL device of the present invention in order to emit light efficiently, it is desirable that at least one surface be sufficiently transparent in the light emission wavelength region of the device.
  • the substrate is also preferably transparent.
  • the transparent electrode is set using the above-described conductive material so that predetermined translucency is ensured by a method such as vapor deposition or sputtering.
  • a hole injection material a compound having the ability to transport holes, the hole injection effect from the anode, the hole injection effect excellent for the light emitting layer or the light emitting material, and the thin film forming ability Is preferred.
  • a more effective hole injection material is a phthalocyanine derivative.
  • phthalocyanine (Pc) derivatives examples include H2Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl2SiPc, (HO) AlPc, (HO) GaPc, VOPc, and OPP Examples include, but are not limited to, phthalocyanine derivatives and naphthalocyanine derivatives such as MoOPc and GaPc-O-GaPc.
  • carriers can be sensitized by adding an electron acceptor such as a TCNQ derivative to the hole injection material.
  • a preferred hole transport material that can be used in the organic EL device of the present invention is an aromatic tertiary amine derivative.
  • the aromatic tertiary amine derivative include N, N′-diphenyl-N, N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine, N, N, N ′, N′-tetra Biphenyl-1,1′-biphenyl-4,4′-diamine or the like, or an oligomer or polymer having an aromatic tertiary amine skeleton is not limited thereto.
  • the following electron injection materials are used for the electron injection / transport layer.
  • the electron injecting material a compound having an ability to transport electrons, an electron injecting effect from the cathode, an excellent electron injecting effect for the light emitting layer or the light emitting material, and an excellent thin film forming ability is preferable.
  • more effective electron injection materials are metal complex compounds and nitrogen-containing heterocyclic derivatives.
  • the metal complex compound include 8-hydroxyquinolinate lithium, bis (8-hydroxyquinolinato) zinc, tris (8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis. (10-Hydroxybenzo [h] quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, and the like are exemplified, but not limited thereto.
  • nitrogen-containing heterocyclic derivative for example, oxazole, thiazole, oxadiazole, thiadiazole, triazole, pyridine, pyrimidine, triazine, phenanthroline, benzimidazole, imidazopyridine and the like are preferable, and among them, benzimidazole derivative, phenanthroline derivative, imidazopyridine Derivatives are preferred.
  • a preferred form of the organic EL device of the present invention includes a form in which at least one of an electron donating dopant and an organometallic complex is further contained in these electron injection materials. More preferably, in order to facilitate reception of electrons from the cathode, at least one of an electron donating dopant and an organometallic complex is doped in the vicinity of the interface between the organic thin film layer and the cathode. According to such a configuration, it is possible to improve the light emission luminance and extend the life of the organic EL element.
  • the electron donating dopant include at least one selected from alkali metals, alkali metal compounds, alkaline earth metals, alkaline earth metal compounds, rare earth metals, rare earth metal compounds, and the like.
  • the organometallic complex include at least one selected from an organometallic complex containing an alkali metal, an organometallic complex containing an alkaline earth metal, an organometallic complex containing a rare earth metal, and the like.
  • alkali metal examples include lithium (Li) (work function: 2.93 eV), sodium (Na) (work function: 2.36 eV), potassium (K) (work function: 2.28 eV), rubidium (Rb) (work Function: 2.16 eV), cesium (Cs) (work function: 1.95 eV) and the like, and those having a work function of 2.9 eV or less are particularly preferable.
  • K, Rb, and Cs are preferred, Rb or Cs is more preferred, and Cs is most preferred.
  • alkaline earth metal examples include calcium (Ca) (work function: 2.9 eV), strontium (Sr) (work function: 2.0 eV to 2.5 eV), barium (Ba) (work function: 2.52 eV).
  • a work function of 2.9 eV or less is particularly preferable.
  • the rare earth metal examples include scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb) and the like, and those having a work function of 2.9 eV or less are particularly preferable.
  • preferred metals are particularly high in reducing ability, and by adding a relatively small amount to the electron injection region, it is possible to improve the light emission luminance and extend the life of the organic EL element.
  • alkali metal compound examples include lithium oxide (Li 2 O), cesium oxide (Cs 2 O), alkali oxides such as potassium oxide (K 2 O), lithium fluoride (LiF), sodium fluoride (NaF), fluorine.
  • alkali halides such as cesium fluoride (CsF) and potassium fluoride (KF), and lithium fluoride (LiF), lithium oxide (Li 2 O), and sodium fluoride (NaF) are preferable.
  • alkaline earth metal compound examples include barium oxide (BaO), strontium oxide (SrO), calcium oxide (CaO), and barium strontium oxide (Ba x Sr 1-x O) (0 ⁇ x ⁇ 1), Examples thereof include barium calcium oxide (Ba x Ca 1-x O) (0 ⁇ x ⁇ 1), and BaO, SrO, and CaO are preferable.
  • the rare earth metal compound ytterbium fluoride (YbF 3), scandium fluoride (ScF 3), scandium oxide (ScO 3), yttrium oxide (Y 2 O 3), cerium oxide (Ce 2 O 3), gadolinium fluoride (GdF 3), such as terbium fluoride (TbF 3) can be mentioned, YbF 3, ScF 3, TbF 3 are preferable.
  • the organometallic complex is not particularly limited as long as it contains at least one of alkali metal ions, alkaline earth metal ions, and rare earth metal ions as metal ions.
  • the ligands include quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiaryloxadiazole, hydroxydiarylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, Hydroxyfulborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, ⁇ -diketones, azomethines, and derivatives thereof are preferred, but not limited thereto.
  • the electron donating dopant and the organometallic complex may be used singly or in combination of two or more.
  • Each layer of the organic EL device of the present invention can be formed by any of dry deposition methods such as vacuum deposition, sputtering, plasma, and ion plating, and wet deposition methods such as spin coating, dipping, flow coating, and inkjet. can do.
  • the material for forming each layer is dissolved or dispersed in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane or the like to form a thin film, and any solvent may be used.
  • an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane or the like
  • any solvent may be used.
  • an organic EL material-containing solution containing the aromatic amine derivative of the present invention and a solvent can be used as a material for an organic EL element.
  • an appropriate resin or additive may be used for improving the film formability and preventing pinholes in the film.
  • the film thickness is not particularly limited, but must be set to an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied.
  • the normal film thickness is suitably in the range of 5 nm to 10 ⁇ m, but more preferably in the range of 10 nm to 0.2 ⁇ m.
  • the present invention is not limited to the above-described embodiment, but includes modifications and improvements as long as the object of the present invention can be achieved.
  • a light emitting material in addition to at least one selected from the aromatic amine derivatives represented by the general formula (1), a light emitting material, a doping material, a hole injection material, At least one of the hole transport material and the electron injection material may be contained in the same layer.
  • a protective layer is provided on the surface of the device, or the entire device is protected by silicon oil, resin, etc. It is also possible to do.
  • the configuration of the organic EL element is not limited to the configuration example of the organic EL element 1 shown in FIG.
  • an electron barrier layer may be provided on the anode side of the light emitting layer
  • a hole barrier layer may be provided on the cathode side of the light emitting layer.
  • the light emitting layer is not limited to one layer, and a plurality of light emitting layers may be stacked.
  • the organic EL element has a plurality of light emitting layers, it is preferable that at least one light emitting layer contains the aromatic amine derivative of the present invention.
  • the other light emitting layer may be a fluorescent light emitting layer that includes a fluorescent light emitting material and emits fluorescence, or may be a phosphorescent light emitting layer that includes a phosphorescent light emitting material and emits phosphorescence.
  • these light emitting layers may be provided adjacent to each other, or may be laminated via other layers (for example, charge generation layers). .
  • the bromide 1 (2.5 g (6 mmol)) and dehydrated xylene (100 mL) were added to a 300 mL three-necked flask and cooled to ⁇ 30 ° C. After cooling, 4.5 mL of n-butyllithium (1.6 M hexane solution) was added and reacted for 1 hour. After completion of the reaction, the mixture was cooled to ⁇ 70 ° C., and after cooling, 1.6 mL of triisopropyl borate was added. The temperature was raised slowly, and the mixture was stirred at room temperature for 1 hour. After stirring, 20 mL of 10% hydrochloric acid solution was further added and stirred.
  • n-butyllithium 1.6 M hexane solution
  • Example 1 A transparent electrode made of indium tin oxide having a thickness of 120 nm was provided on a glass substrate having a size of 25 mm ⁇ 75 mm ⁇ 1.1 mm. This transparent electrode serves as an anode. Subsequently, the glass substrate was cleaned by irradiating with ultraviolet rays and ozone, and then placed in a vacuum deposition apparatus. First, N ′, N ′′ -bis [4- (diphenylamino) phenyl] -N ′, N ′′ -diphenylbiphenyl-4,4′-diamine was deposited to a thickness of 60 nm, and a hole injection layer was formed. Formed.
  • Example 1 was produced.
  • the organic EL element of Example 1 was driven at a current density of 10 mA / cm 2 , blue light emission was observed.
  • Compound 1 was confirmed to be useful as an organic EL device material.
  • Example 2 The organic EL element of Example 2 was produced in the same manner as in Example 1 except that EM2 which is the host material of the organic EL element of Example 1 was changed to EM367. The organic EL element of Example 2 was driven at a current density of 10 mA / cm 2 in the same manner as the organic EL element of Example 1. As a result, blue light emission was also observed for the organic EL device of Example 2. Thus, Compound 1 was confirmed to be useful as an organic EL device material.
  • aromatic amine derivative of this invention although the example which light-emitted blue in the said Example is shown, it is not limited to this.
  • An aromatic amine derivative having a structure in which an aryl group or the like is directly bonded to a pyrene ring can emit green light.
  • the compounds 204 to 211 are mentioned.
  • the organic EL device of the present invention can be used for a flat light emitter such as a flat panel display of a wall-mounted television, a copying machine, a printer, a light source such as a backlight of a liquid crystal display or instruments, a display board, a marker lamp, and the like.
  • a flat light emitter such as a flat panel display of a wall-mounted television, a copying machine, a printer, a light source such as a backlight of a liquid crystal display or instruments, a display board, a marker lamp, and the like.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Furan Compounds (AREA)

Abstract

L'invention concerne un dérivé d'amine aromatique représenté par la formule générale (1). Dans la formule générale (1), R2, R3, R4, R5, R7, R8, R9 et R10 représentent chacun indépendamment un atome d'hydrogène ou un groupe substituant. Dans la formule générale (1), R1 et R6 sont représentés par la formule générale (2); L1 et L2 représentent chacun indépendamment une liaison simple, le résidu divalent d'un groupe aryle ou analogue; et L3 représente le résidu divalent d'un groupe aryle ou analogue. Dans la formule générale (2), Ar1 représente un groupe substituant monovalent représenté par la formule générale (3), qui forme une structure partielle; X représente un atome d'oxygène ou un atome de soufre; et A et B représentent un noyau à six chaînons. Dans la formule générale (2), Ar2 représente un groupe aryle ou un groupe substituant monovalent ou analogue représenté par la formule générale (3), qui forme une structure partielle.
PCT/JP2012/074232 2011-09-22 2012-09-21 Dérivé d'amine aromatique et élément électroluminescent organique utilisant celui-ci WO2013042769A1 (fr)

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WO2013042775A1 (fr) * 2011-09-22 2013-03-28 出光興産株式会社 Dérivé d'amine aromatique et élément électroluminescent organique l'employant
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